WO2008154234A2 - Extended release formulation of nevirapine - Google Patents
Extended release formulation of nevirapine Download PDFInfo
- Publication number
- WO2008154234A2 WO2008154234A2 PCT/US2008/065705 US2008065705W WO2008154234A2 WO 2008154234 A2 WO2008154234 A2 WO 2008154234A2 US 2008065705 W US2008065705 W US 2008065705W WO 2008154234 A2 WO2008154234 A2 WO 2008154234A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nevirapine
- hours
- released
- geometric mean
- exhibits
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Definitions
- the invention relates to a pharmaceutical composition comprising nevirapine.
- Nevirapine or 11 -cyclopropyl-5, 11 -dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'- e][1 ,4]diazepin-6-one, is a known agent for the treatment of infection by HIV-1 (human immunodeficiency virus, type 1 ), which acts through specific inhibition of HIV-1 reverse transcriptase. Its synthesis and use are described in various publications including, inter alia, U.S. Patent 5,366,972 and European Patent 0429987B1. Viramune® tablets, a drug product comprising nevirapine, has been approved, in many countries, for use in the treatment of HIV-1 infection.
- Viramune® tablets is an immediate release (IR) formulation that is intended to be administered twice daily in order to maintain a therapeutically appropriate blood level of the active ingredient, nevirapine.
- IR immediate release
- XR extended release
- nevirapine possesses physicochemical properties that would call into question the feasibility of an XR formulation. More particularly, it will be appreciated that XR formulations are generally designed to be gradually absorbed during transit through the intestines, where the pH is high. Nevirapine is a weak base, and it accordingly can be expected to exhibit low solubility in the intestines. (Nevirapine is a Class Il drug substance according to the Biopharmaceutics Classification System.) For this reason, it is reasonable to expect that an XR formulation of nevirapine might transit the Gl tract and be excreted without sufficient dissolution and absorption of the nevirapine. This would make an XR formulation unworkable.
- Any extended release (XR) formulation would have to exhibit a peak/trough ratio that is equal to or even less than that of the IR formulation administered twice daily, despite once daily administration of the XR. Otherwise, with a larger peak/trough ratio than observed with IR, the XR formulation would likely be inferior in its clinical risk/benefit profile.
- the present invention is an extended release (XR) formulation of nevirapine that is suitable for administration only once per day, while still maintaining a therapeutically appropriate blood level of the active ingredient.
- Figures 1 and 2 respectively show the concentration of nevirapine in the blood plasma, as a function of time, obtained by the administration to healthy subjects of a single 400 mg or 300 mg tablet extended release dosage form of nevirapine in accordance with the present invention.
- Figure 3 depicts the steady state concentration of nevirapine in the blood plasma, as a function of time, obtained by repeated once daily administration to healthy subjects of 400 mg tablet extended release dosage forms of nevirapine in accordance with the invention.
- Figure 4 depicts the dissolution profile of the extended release formulation according to the invention.
- the extended release formulation provided by the invention exhibits, after administration of a single dose in fasted state to a healthy volunteer, a distinctive pharmacokinetic profile that is characterized by the following two parameters for a dosage form comprising 300 mg of nevirapine:
- the extended release formulation provided by the invention is further characterized by a geometric mean T max of 10 to 48 hr (again, after single dose administration in fasted state).
- the extended release formulation provided by the invention is additionally characterized by the following PK parameters observed after repeated once- daily dosing under steady state conditions: For a 300 mg dose: (a) a geometric mean C ma ⁇ ,ss of 2,300 to 3,700 ng/mL; and
- the above noted multiple-dose PK parameters are measured while fasting, during a 24 hour interval after plasma levels of the drug have reached steady state conditions.
- the extended release formulation provided by the invention is further characterized by exhibiting a very narrow ratio of C ma ⁇ ,ss/Cm ⁇ n,ss which is in the range of 1.1 to 2, for both the 300 and 400 mg doses, with said parameter being measured during steady state.
- PK parameters are to be obtained from observed data and not modeled data.
- the extended release formulation of the invention is characterized by having an in vitro dissolution profile such that at least 2% w/w and no more than 30% w/w of the nevirapine is released at 2 hours; at least 20% w/w and up to 100% w/w of the nevirapine is released at 8 hours; at least 40% w/w and and up to 100% w/w of the nevirapine is released at 14 hours, when dissolution is measured by the USP Paddle Method at 50 rpm at a volume of 900 mL aqueous buffer containing 6% w/w of sodium lauryl sulfate, having a pH of 6.8 at 37°C.
- the extended release formulation of the invention is characterized by having an in vitro dissolution profile such that at least 5% w/w and no more than 20% w/w of the nevirapine is released at 2 hours; at least 30% w/w and no more than 80% w/w of the nevirapine is released at 8 hours; at least 50% w/w and and up to 100% w/w of the nevirapine is released at 14 hours, when dissolution is measured by the USP Paddle Method at 50 rpm at a volume of 900 ml_ aqueous buffer containing 6% w/w of sodium lauryl sulfate, having a pH of 6.8 at 37°C.
- the extended release formulation of the invention is characterized by having an in vitro dissolution profile such that at least 8% w/w and no more than 15% w/w of the nevirapine is released at 2 hours; at least 45% w/w and no more than 60% w/w of the nevirapine is released at 8 hours; at least 75% w/w and and no more than 95% w/w of the nevirapine is released at 14 hours, when dissolution is measured by the USP Paddle Method at 50 rpm at a volume of 900 ml_ aqueous buffer containing 6% w/w of sodium lauryl sulfate, having a pH of between 6.8 at 37°C.
- the pharmaceutical composition of the invention may be formulated by combining nevirapine with conventional carriers or excipients.
- Preferred embodiments of the invention are tablets.
- an extended release matrix which comprises a hydrophilic polymer which imparts controlled release of the nevirapine.
- the hydrophilic polymer can be, but is not limited to hydroxypropylmethylcellulose (HPMC, also known as hypromellose), hydroxypropylcellulose (HPC), hydroxyethylcellulose (HEC), xanthan gum, sodium alginate, polyethylene oxide, and crosslinked homopolymers and copolymers of acrylic acid. Mixtures of the foregoing hydrophilic polymers may also be used.
- HPMC hyperromellose
- HPMC hyperromellose
- the formulation provided by the invention can optionally also include other conventional excipients such as fillers, diluents, glidents and binders.
- the formulation provided by the invention can be prepared by mixing the individual components (nevirapine drug substance, hydrophilic polymer(s) and optional filler(s), diluent(s), glidant(s) and binder(s)) and then granulating with a granulation solution until complete. The granulation is then dried. The dried granulation is milled, combined with lubricant and mixed to prepare the final blend for compression into tablets. Tablets are compressed by a force of about 10-25 kN, preferably 11 -19 kN, and more preferably 13-17 kN into desirable sizes and shapes of hardness from about 11-26 kP, preferably 16-21 kP.
- Formulations comprising an extended release matrix comprising between about 20% and 25% by weight of hypromellose are preferred.
- Hypromellose 2208 (MethocelTM K4M Premium CR).
- each tablet comprises:
- each tablet is compressed by a force of about10-25 kN.
- Example 1 The invention can be further understood by way of the following non-limiting examples, which describe specific tablet formulations.
- Example 1
- lactose, nevirapine drug substance and hypromellose are mixed and then granulated with water until complete.
- the granulation is then dried.
- the dried granulation is milled, combined with lubricant (magnesium stearate) and mixed to prepare the final blend for compression into tablets. Tablets are compressed by a force of about 10-25 kN into 9.3 x 19.0 mm tablets.
- lactose, nevirapine drug substance and hypromellose are mixed and then granulated with water until complete.
- the granulation is then dried.
- the dried granulation is milled, combined with lubricant (magnesium stearate) and mixed to prepare the final blend for compression into tablets. Tablets are compressed by a force of about 10-25 kN into 9.3 x 19.0 mm tablets.
- lactose, nevirapine drug substance and hypromellose are mixed and then granulated with water until complete.
- the granulation is then dried.
- the dried granulation is milled, combined with lubricant (magnesium stearate) and mixed to prepare the final blend for compression into tablets. Tablets are compressed into 9.3 x 19.0 mm tablets.
- the lactose, nevirapine drug substance and hypromellose are mixed and then granulated with water until complete.
- the granulation is then dried.
- the dried granulation is milled, combined with lubricant (magnesium stearate) and mixed to prepare the final blend for compression into tablets. Tablets are compressed by a force of about 10-25 kN into 9.3 x 19.0 mm tablets.
- lubricant magnesium stearate
- gMean geometric mean
- gCV geometric CV
- the USP paddle method is the paddle method described, e.g., in U.S. Pharmacopoeia XXII (1990).
- USP Apparatus I (baskets) at 50 rpm in 900 ml_ medium at 37°C. Baskets (#10 mesh) were chosen to assure that the tablets would not stick to the bottom of the vessel and thereby minimize surface area available to solution during testing.
- Drug substance dissolution rate was measured using an on-line Cary 50 UV- Visible Spectrophotometer (Varian Australia Pty LTD) at 330 nm against external standards.
- the tested dissolution media 0.05M phosphate buffer (NaH2PO4/NaOH or NaH2PO4/Na2HPO4/NaOH - all EM Science, Darmstadt, Germany) containing 6% Sodium Lauryl Sulfate (13% Sodium Lauryl Sulfate in deionized water, Anachemia Chemicals, Rouses Point, NY or Sodium Lauryl Sulfate, Spectrum Chemical MFG. CORP.) and adjusted to pH 6.8.
- 0.05M phosphate buffer NaH2PO4/NaOH or NaH2PO4/Na2HPO4/NaOH - all EM Science, Darmstadt, Germany
- 6% Sodium Lauryl Sulfate (13% Sodium Lauryl Sulfate in deionized water, Anachemia Chemicals, Rouses Point, NY or Sodium Lauryl Sulfate, Spectrum Chemical MFG. CORP.
- Dissolution was performed using 10 mesh stainless steel baskets. Dissolution parameters:
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK08756672.5T DK2155169T3 (en) | 2007-06-08 | 2008-06-04 | Formulation of nevirapine extended release |
BRPI0811732-2A2A BRPI0811732A2 (pt) | 2007-06-08 | 2008-06-04 | Formulação de liberação prolongada de nevirapina |
US12/523,226 US8460704B2 (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
MX2009007764A MX2009007764A (es) | 2007-06-08 | 2008-06-04 | Formulacion de nevirapina de liberacion prolongada. |
EA200900958A EA018377B1 (ru) | 2007-06-08 | 2008-06-04 | Препарат невирапина пролонгированного высвобождения |
CA2687491A CA2687491C (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
CN2008800193577A CN101784263B (zh) | 2007-06-08 | 2008-06-04 | 奈韦拉平的延长释放制剂 |
NZ578664A NZ578664A (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
JP2009552940A JP5417662B2 (ja) | 2007-06-08 | 2008-06-04 | ネビラピンの徐放性製剤 |
UAA200908230A UA97971C2 (ru) | 2007-06-08 | 2008-06-04 | Препарат невирапина пролонгированного высвобождения |
EP08756672.5A EP2155169B1 (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
ES08756672.5T ES2574836T3 (es) | 2007-06-08 | 2008-06-04 | Formulación de liberación prolongada de nevirapina |
AU2008262031A AU2008262031B2 (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
IL199924A IL199924A0 (en) | 2007-06-08 | 2009-07-16 | Extended relase formulation of nevirapine |
TNP2009000510A TN2009000510A1 (en) | 2007-06-08 | 2009-12-04 | Extended release formulation of nevirapine |
MA32400A MA31430B1 (fr) | 2007-06-08 | 2009-12-07 | Formulation a liberation prolongee de nevirapine |
HK11100032.7A HK1145806A1 (en) | 2007-06-08 | 2011-01-05 | Extended release formulation of nevirapine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US94276507P | 2007-06-08 | 2007-06-08 | |
US60/942,765 | 2007-06-08 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2008154234A2 true WO2008154234A2 (en) | 2008-12-18 |
WO2008154234A9 WO2008154234A9 (en) | 2009-11-26 |
WO2008154234A3 WO2008154234A3 (en) | 2010-01-21 |
Family
ID=39739795
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/065705 WO2008154234A2 (en) | 2007-06-08 | 2008-06-04 | Extended release formulation of nevirapine |
Country Status (29)
Country | Link |
---|---|
US (1) | US8460704B2 (es) |
EP (1) | EP2155169B1 (es) |
JP (1) | JP5417662B2 (es) |
KR (1) | KR101017862B1 (es) |
CN (1) | CN101784263B (es) |
AR (1) | AR066924A1 (es) |
AU (1) | AU2008262031B2 (es) |
BR (1) | BRPI0811732A2 (es) |
CA (1) | CA2687491C (es) |
CL (1) | CL2008001678A1 (es) |
CO (1) | CO6150128A2 (es) |
DK (1) | DK2155169T3 (es) |
EA (1) | EA018377B1 (es) |
EC (1) | ECSP099561A (es) |
ES (1) | ES2574836T3 (es) |
HK (1) | HK1145806A1 (es) |
HU (1) | HUE028598T2 (es) |
IL (1) | IL199924A0 (es) |
MA (1) | MA31430B1 (es) |
MX (1) | MX2009007764A (es) |
NZ (1) | NZ578664A (es) |
PE (2) | PE20090371A1 (es) |
PL (1) | PL2155169T3 (es) |
TN (1) | TN2009000510A1 (es) |
TW (1) | TWI419716B (es) |
UA (1) | UA97971C2 (es) |
UY (1) | UY31128A1 (es) |
WO (1) | WO2008154234A2 (es) |
ZA (1) | ZA200904939B (es) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012164241A1 (en) | 2011-05-30 | 2012-12-06 | Cipla Limited | Pharmaceutical antiretroviral composition |
US8460704B2 (en) | 2007-06-08 | 2013-06-11 | Boehringer Ingelheim International Gmbh | Extended release formulation of nevirapine |
CN104523630A (zh) * | 2015-01-22 | 2015-04-22 | 山东新时代药业有限公司 | 一种奈韦拉平片剂 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY149159A (en) | 2005-11-15 | 2013-07-31 | Hoffmann La Roche | Method for treating joint damage |
US8178495B2 (en) | 2008-06-27 | 2012-05-15 | Duke University | Therapeutic agents comprising a GLP-1 receptor agonist and elastin-like peptide |
US20130172274A1 (en) | 2005-12-20 | 2013-07-04 | Duke University | Methods and compositions for delivering active agents with enhanced pharmacological properties |
CN104023784B (zh) * | 2011-08-24 | 2018-05-25 | 费斯生物制药公司 | 供持续释放的活性剂制剂 |
BR112014021927A2 (pt) * | 2012-03-05 | 2019-09-24 | Cipla Ltd | composição farmacêutica antirretroviral, processo para preparar uma composição farmacêutica antirretroviral, método para o tratamento ou profilaxia de doenças causadas por retrovírus, e, uso de lamivudina, festinavir e nevirapina |
EP3153157A1 (en) | 2015-10-09 | 2017-04-12 | Teva Pharmaceutical Works Private Limited Company | Pharmaceutical composition for prolonged release of nevirapine |
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WO2000035419A2 (en) * | 1998-12-17 | 2000-06-22 | Alza Corporation | Conversion of liquid filled gelatin capsules into controlled release systems by multiple coatings |
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WO2007047371A2 (en) * | 2005-10-14 | 2007-04-26 | Microdose Technologies, Inc. | Pharmaceutical packaging of an oral dosage combination |
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US5366972A (en) * | 1989-04-20 | 1994-11-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | 5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection |
US5133974A (en) * | 1989-05-05 | 1992-07-28 | Kv Pharmaceutical Company | Extended release pharmaceutical formulations |
CA2030056C (en) | 1989-11-17 | 1995-10-17 | Karl D. Hargrave | 5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepines and their use in the prevention or treatment of hiv infection |
US5419917A (en) * | 1994-02-14 | 1995-05-30 | Andrx Pharmaceuticals, Inc. | Controlled release hydrogel formulation |
WO1999029297A1 (en) * | 1997-12-05 | 1999-06-17 | Alza Corporation | Osmotic dosage form comprising first and second coats |
BR0009437A (pt) * | 1999-03-31 | 2002-01-15 | Janssen Pharmaceutica Nv | Amido pré-gelatinizado em uma formulação de liberação controlada |
NZ517025A (en) * | 1999-09-24 | 2003-07-25 | Janssen Pharmaceutica Nv | Antiviral compositions |
EP1239840B1 (en) | 1999-12-09 | 2005-04-06 | Alza Corporation | Antiviral medication |
WO2002092095A1 (en) | 2001-05-11 | 2002-11-21 | Boehringer Ingelheim International Gmbh | Use of nevirapine to treat or prevent lipid pathology in patients with hiv that is resistant to nevirapine |
US20030050620A1 (en) | 2001-09-07 | 2003-03-13 | Isa Odidi | Combinatorial type controlled release drug delivery device |
AU2003287666A1 (en) | 2002-11-13 | 2004-06-03 | Control Delivery Systems, Inc. | Systemic delivery of antiviral agents |
US20070259014A1 (en) | 2003-06-20 | 2007-11-08 | Vgx Pharmaceuticals, Inc. | Compositions for and Methods for Treating Hiv |
EA008944B1 (ru) | 2003-10-01 | 2007-10-26 | Люпин Лимитед | Фармацевтическая композиция управляемого высвобождения и способ ее получения |
PL1696822T3 (pl) | 2003-11-13 | 2010-08-31 | Psivida Inc | Wstrzykiwane implanty o opóźnionym wydzielaniu mające matrycę rdzenia i powłokę podatne na erozję biologiczną |
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ES2574836T3 (es) | 2007-06-08 | 2016-06-22 | Boehringer Ingelheim International Gmbh | Formulación de liberación prolongada de nevirapina |
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2008
- 2008-06-04 ES ES08756672.5T patent/ES2574836T3/es active Active
- 2008-06-04 BR BRPI0811732-2A2A patent/BRPI0811732A2/pt not_active IP Right Cessation
- 2008-06-04 KR KR1020097016610A patent/KR101017862B1/ko active IP Right Grant
- 2008-06-04 MX MX2009007764A patent/MX2009007764A/es active IP Right Grant
- 2008-06-04 EP EP08756672.5A patent/EP2155169B1/en not_active Revoked
- 2008-06-04 WO PCT/US2008/065705 patent/WO2008154234A2/en active Application Filing
- 2008-06-04 DK DK08756672.5T patent/DK2155169T3/en active
- 2008-06-04 HU HUE08756672A patent/HUE028598T2/en unknown
- 2008-06-04 PL PL08756672.5T patent/PL2155169T3/pl unknown
- 2008-06-04 NZ NZ578664A patent/NZ578664A/en not_active IP Right Cessation
- 2008-06-04 JP JP2009552940A patent/JP5417662B2/ja active Active
- 2008-06-04 US US12/523,226 patent/US8460704B2/en active Active
- 2008-06-04 CA CA2687491A patent/CA2687491C/en active Active
- 2008-06-04 EA EA200900958A patent/EA018377B1/ru not_active IP Right Cessation
- 2008-06-04 UA UAA200908230A patent/UA97971C2/ru unknown
- 2008-06-04 AU AU2008262031A patent/AU2008262031B2/en not_active Ceased
- 2008-06-04 CN CN2008800193577A patent/CN101784263B/zh active Active
- 2008-06-06 CL CL2008001678A patent/CL2008001678A1/es unknown
- 2008-06-06 UY UY31128A patent/UY31128A1/es not_active Application Discontinuation
- 2008-06-06 TW TW097121294A patent/TWI419716B/zh active
- 2008-06-06 AR ARP080102446A patent/AR066924A1/es unknown
- 2008-06-06 PE PE2008000969A patent/PE20090371A1/es not_active Application Discontinuation
- 2008-06-06 PE PE2013000070A patent/PE20131035A1/es not_active Application Discontinuation
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2009
- 2009-07-15 ZA ZA200904939A patent/ZA200904939B/xx unknown
- 2009-07-16 IL IL199924A patent/IL199924A0/en unknown
- 2009-07-21 CO CO09075419A patent/CO6150128A2/es unknown
- 2009-08-05 EC EC2009009561A patent/ECSP099561A/es unknown
- 2009-12-04 TN TNP2009000510A patent/TN2009000510A1/fr unknown
- 2009-12-07 MA MA32400A patent/MA31430B1/fr unknown
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2011
- 2011-01-05 HK HK11100032.7A patent/HK1145806A1/xx unknown
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WO2000035419A2 (en) * | 1998-12-17 | 2000-06-22 | Alza Corporation | Conversion of liquid filled gelatin capsules into controlled release systems by multiple coatings |
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WO2007047371A2 (en) * | 2005-10-14 | 2007-04-26 | Microdose Technologies, Inc. | Pharmaceutical packaging of an oral dosage combination |
Non-Patent Citations (1)
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US8460704B2 (en) | 2007-06-08 | 2013-06-11 | Boehringer Ingelheim International Gmbh | Extended release formulation of nevirapine |
WO2012164241A1 (en) | 2011-05-30 | 2012-12-06 | Cipla Limited | Pharmaceutical antiretroviral composition |
CN104523630A (zh) * | 2015-01-22 | 2015-04-22 | 山东新时代药业有限公司 | 一种奈韦拉平片剂 |
CN104523630B (zh) * | 2015-01-22 | 2017-08-25 | 山东新时代药业有限公司 | 一种奈韦拉平片剂 |
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